DE2047695C3 - Electrophotographic recording material - Google Patents

Description

which is a bis (N, N-dialkylaminophenyl) methao, contains a binder and optionally a sensitizing dye, and is thereby characterized in that the photoconductive layer is a compound of the formula as photoconductor

N-

⁵ X

R ₇

contains, wherein R ₁ , R _s , R ₃ and R ₄ each equal to an optionally substituted alkyl group having 1 to 18 carbon atoms, R ₅ and R ₆ each equal to a hydrogen or halogen atom or an optionally substituted aliphatic alkyl or alkoxy group and R ₇ and ^R * J ^ewei k are an optionally substituted alkyl group having 1 to 18 carbon atoms or an optionally substituted cycloalkyl group or together are equal to an optionally substituted cycloalkylidene group.

The invention achieves that electrophotographic Recording materials are created which differ from corresponding recording materials of the prior art through improved sensitivity and light stability distinguish. Surprisingly, it has been shown that with known photoconductors, the central Methyl carbon atom not as in the case of the invention photoconductors used is substituted, can not achieve the sensitivities that are achieved when using the photoconductor used according to the invention can be achieved.

The increased sensitivity of the electrophotographic recording materials according to the invention to Corresponding known recording materials can be recognized when an inventive Recording material to an appropriate potential, e.g. B. 500 to 600 volts, is charged. the The relative sensitivity of such a recording material results from the inverse of the exposure, which is required to reduce the potential of the surface charge to 100 volts. The diminution of the surface potential to about 100 volts or below is significant because this decrease surface potential is a requirement for satisfactory electrostatic development Image is. The relative sensitivity of an electrophotographic recording material at 100 volts is thus a measure of the usefulness of the electrophotographic recording material for making pictures. It has been shown that when many common photoconductors are used, the surface potential often cannot be reduced to or below 100 volts, which is why such recording materials no sensitivity value can be assigned. Only when it is possible It is possible to reduce the surface potential to 100 volts or below, since the recording material to be assessed by a defined sensitivity. As already said, are distinguished according to the invention used photoconductors from the fact that they increased the recording materials Give sensitivity.

In the structural formula given, R ₁ , R ₂ , R ₃ and R _{4 can represent} , for example, methyl, ethyl, propyl, pentyl, hexyl, isobutyl, 3-methylpentyl or octyl groups.

If R ₅ and R ₆ are alkyl groups, these preferably have 1 to 18 carbon atoms

and consist, for example, of those alkyl groups as specified _{for R 1} , R * R, and R _4. If R ₅ and R ₆ are alkoxy groups, then these likewise preferably have 1 to 18 carbon atoms and «stenen

ίο, for example, from methoxy, ethoxy, propoxy or butoxy groups. If R _s and R ₆ represent halogen atoms, these can consist of Cnior, bromine, fluorine or iodine atoms. If R ₇ and R _{8 have} the meaning of alkyl groups,

for example, these can consist of methyl, atnyi, propyl, butyl, isobutyl, octyl or dodecyl groups. Typical substituted alkyl groups that R ₇ and R _s can represent are, for example:

a) alkoxyalkyl groups, e.g. B. ethoxypropyl, methoxy butyl or propoxymethyl groups;

b) aryloxyalkyl groups, e.g. B. phenoxyethyl, naphthoxymethyl or phenoxypentyl groups;

c) aminoalkyl groups, e.g. B. aminobutyl, aminoethyl or aminopropyl groups;

d) hydroxyalkyl groups, e.g. B. hydroxypropyl, Hyuroxyoctyl or hydroxymethyl groups;

e) aralkyl groups, e.g. B. benzyl or phenethyl groups;

f) alkylaminoalkyl groups, e.g. B. methylaminopropyl, methylaminoethyl or dialkylaminoalkyl groups, z. B. diethylaminoethyl, dimethylaminopropyl or dipropylaminooctyl groups;

g) arylaminoalkyl groups, e.g. B. phenylaminoalkyl-, diphenylaminoalkyl, N - phenyl- N-ethylaminopentyl-, N-phenyl-N-ethylaminohexyl or naphthylaminomethylgrappen;

h) nitroalkyl groups, e.g. B. nitrobutyl, nitroethyl

or nitropentyl groups;
i) cyanoalkyl groups, e.g. B. cyanopropyl, cyano

butyl or cyanoethyl groups; j) haloalkyl groups, e.g. B. chloromethyl, bromo-

pentyl or chlorooctyl groups; k) alkyl groups represented by an acyl group of the

following formula

-C-R

su "t: -rri. are, where R means: a hydrogen bond '.'. i :! or a hydroxy group or an aryl group, e.g. B. a phenyl or naphthyl group or a short-chain alkyl group with preferably 1 to 8 carbon atoms, ζ. Β. one Methyl, ethyl or propyl group or an optionally substituted amino group, e.g. an amino group substituted by two short-chain alkyl groups, a short-chain alkoxy group with preferably 1 to 8 carbon atoms, ζ. B. a butoxy or methoxy group or an aryloxy group, e.g. B. a phenoxy or naphthoxy group. ,

If R ₇ and R _{8 have} the meaning * if optionally substituted cycloalkyl groups, then these preferably have 4 to 8 ring carbon atoms and consist, for example, of optionally substituted

tuted cyclobutyl, cyclohexyl or cyclopentyl groups.

Typical substituted cycloalkyl groups are:

a) alkoxycycloalkyl groups, e.g. B. ethoxycyclohexyl, Methoxycyclobatyl or propoxycydohexyl groups;

b) aryloxycycloalkyl groups, e.g. B. Phenoxycyclohexyl-, Naphthoxycyclohexyl or phenoxycyclopentyl groups;

c) aminocydoalkyl groups, ζ. B. aminocyclobutyl, Aminocyclohexyl or aminocyclopentyl groups;

d) hydroxycycloalkyl groups, e.g. B. Hydroxycyclohexyl, Hydroxycyclopentyl or hydroxycyclobutyl groups;

e) arylcycloalkyl groups, e.g. B. phenylcyclohexyl, or phenylcyclobutyl groups;

f) Alkylaminocycloalkylgrupi ^ en, z. B. Methylaminocyclohexyl- or methylaminocyclopentyl groups or dialkylaminocycloalkyl groups, z. B. Diethylaminocyclohexyl, dimethylaminocyclobutyl or dipropylaminocyclooctyl groups;

g) arylaminocycloalkyl groups, e.g. B. phenylaminocyclohexyl, diphenylaminocyclohexyl, N-phenyl-N-ethylaminocyclopentyl, N-phenyl-N-methylaminocyclohexyl or naphthylaminocyclopentyl groups;

h) nitrocycloalkyl groups, e.g. B. nitrocyclobutyl,

Nitrocyclohexyl or nitrocyclopeiityl groups; i) cyanocycloalkyl groups, e.g. B. cyanocyclohexyl,

Cyanocyclobutyl or cyanocyclopentyl groups; j) halocycloalkyl groups, e.g. B. chlorocyclohexyl, Bromocyclopentyl or chlorocyclooctyl

groups;
k) Cycloalkyl groups represented by an acyl group of the formula

-C-R

are substituted, in which R denotes: a hydroxyl group or a hydrogen atom or an aryl group, z. B. a phenyl or naphthyl group or an optionally substituted amino group, z. B. an amino group substituted by two short-chain alkyl groups or one short-chain alkoxy group with 1 to 8 carbon atoms, ζ. B. a methoxy or butoxy group, or an aryloxy group, e.g. B. a phenoxy or naphthoxy group, or a short-chain alkyl group with preferably 1 to 8 carbon atoms, ζ. Β. a methyl, ethyl, propyl or butyl group.

If R ₇ and R ₈ together represent the atoms required to complete an optionally substituted cycloalkylidene group, this cycloalkylidene group preferably has 4 to 20 carbon atoms. The cycloalkylidene group can optionally also be a bridge-containing cycloalkylidene group or a bicycloalkylidene group. Typical, optionally substituted cycloalkylene groups are, for example, optionally substituted cyclobutylidene, cyclopentylidene, cyclohexylidene, cycloheptylidene, norcarylidene, norpinylidene and norbornylidene groups. Typical substituted cycloalkyl groups are, for example:

a) alkoxycycloalkylidene groups, ζ. B. Äthoxycydohexyliden-, Methoxycyclobutyliden-, Pi opoxycyclohexyliden- and methoxynorbornylidene groups;

b) aryloxycycloalkylidene groups, e.g. B. phenoxycyclohexylidene, naphthoxycydohexylidene, Phenoxycyclopentylidene and phenoxynorcarylidene groups;

c) aminocycloalkylidene groups, e.g. B. aminocyclobutylidene-. Aminocyclohexylidene, aminocyclopentylidene, and aminonorpinylidene groups;

d) Hydroxycydoalkylidene groups, e.g. B. Hydroxycydohexylidene, Hydroxycydopentylidene, Hydroxycyclobutyh'den- and Hydroxynorbornylidene groups;

e) alkylcydoalkylidene groups, e.g. B. dimethylcydoalkylidene, Cyclohexylcycloalkylidene, 4- (l ',

'O!', S '^' - tetramethylbutyl-cyclohexylidene groups;

f) arylcycloalkylidene groups, e.g. B. Phenylcyclohexylidene, Phenylcyclobutylidene and Phenylnorcar> lidene groups;

g) alkylaminocycloalkylidene groups, e.g. B. Methyls5 aminocyclohexylidene and methylaminocyclopentylidene groups, and also dialkylaminocycioalcylidene groups, e.g. B. Diethylaminocyclohexylidene, Dimethylammocyclobutylidene, dipropylaminocyclooctylidene, and diethyiaminonorpinylidene groups;

h) arylaminocycloalkylidene groups, e.g. B. Phenylaminocyclohexylidene, Diphenylaminocyclohexylidene -, N- phenyl - N -äthylaminocyclopentylidene -, N-phenyl-N-methylaminocyclohexylidene, naphthylaminocyclopentylidene and phenylaminonorbornylidene groups;

i) nitrocydoalkylidene groups, e.g. B. nitrocyclobutylidene, Nitrocyclohexylidene and nitrocydopentylidene groups;

j) cyanocycloalkylidene groups, e.g. B. cyanocyclohexylidene, Cyanocyclobutylidene and cyanocyclopentylidene groups;

k) halocyeloalkylidene groups, e.g. B. Chlorocyclohexylidene, Bromocyclopentylidene and chlorocyclooctylidene groups;

1) Cycloalkylidene groups represented by an acyl group of the formula

- C - R

are substituted, in which R denotes: a hydrogen atom or a hydroxyl or aryl group, z. B. a phenyl or naphthyl group, or an optionally substituted amino group, e.g. B. an amino group substituted by two short-chain alkyl groups or a short-chain alkoxy group With preferably 1 to 8 carbon atoms, 2 · .. B. a methoxy or butoxy group or an aryloxy group, e.g. B. a phenoxy or naphthoxy group or a short chain alkyl group with preferably 1 to 8 carbon atoms, e.g. B. a methyl, ethyl propyl or elutyl group.

According to a particularly advantageous embodiment of the invention, the photoconductive layer a1 contains: Photoconductor 2,2-bis (4-N, N-diethylaminophenyl) -pro

pan, hereinafter referred to as compound II, 2,2-bis- (4-N, N-diethylaminophenyl) -butane (compound IV), 2,2-bis (4-N, N-diethylaminophenyl) -heptane (Compound V), l, l-bis (4-N, N-diethylaminophenyl) cyclopentane (Compound XVII) or 1,1-bis- (4-N-ethyl-N-methylaminophenyl) -cyclohexane (Compound IX).

Further typical advantageous photoconductors for the production of electrophotographic recording materials according to the invention are listed in Table 1 below.

Table 1

I 2,2-bis (4-N, N-diethylaminophenyl) propane, III l, l-bis (4-N, N-dimethylaminophenyl) -cyclohexane,

VI l, 3,3-tris (4-N, N-diethylaminophenyl) butane,

VII l, l-bis (4-N, N-diethylaminophenyl) -cyclohexane,

VIII l, l-bis (4-N, N-di-n-propyIaminophenyl) -cyclohexane,

X l, l-bis (4-N, N-diethylaminophenyl) -4-methylcyclohexane,

XI l, l-bis (4-N, N-diethylaminophenyl) -3-methylcyclohexane,

XII l, l-bis (4-N, N-diethylaminophenyl) -4- (l '-methylpropyl) cyclohexane,

XIII l, l-bis (4-N, N-diethylaminophenyl) -4- (l ', l', 3 ', 3'-tetramethylbutyl) -cyclohexane,

XIV 1, l-bis (4-N, N-diethylaminophenyl) -3,4-dimethylcyclohexane,

XV l, l-bis (4-N, N-diethylaminophenyl) -3,5-dimethylcyclohexane,

XVI 2- [4,4-bis- (4-N, N-diethylaminophenyl) -cyclohexyli-2-cyclohexylpropane,

XVIII l, l-bis (4-N, N-diethylaminophenyl) -cycloheptane,

XIX 2,2-bis- (4-N, N-diethylaminopbenyl) norbornane,

XX 4,4,4 ', 4'-tetrakis- (4-N, N-diethylaminophenyl) bicyclohexane,

XXI 2,2-bis [4,4-bis (p-N, N-diethylaminophenyl) cyclohexyl] propane,

XXII 2- (4,4 '- [bis (4-N, N-diethylaminophenyl) cyclohexyl]) - 2- (4- [4-N, N-diethylaminophenyl] cyclohex-3-enyl) propane,

XXIII 2 ^ -Bis- (4-N, N-diethylamino-2-chlorophenyl) propane,

XXIV 2,2-bis (4-N, N-diethylamino-2-methoxy) propane.

The electrophotographic recording materials according to the invention can be used in a conventional manner Way to be produced, d. That is, it is first a dispersion or solution of one or more the photoconductor described, a binder and optionally a sensitizer for the photoconductor prepared, whereupon the dispersion or solution is applied to a conventional support. If necessary, they can be used together for the production of the electrophotographic recording materials other known photoconductors are also used with the photoconductors used in accordance with the invention as described, for example, in Belgian patent specification 705117. Possibly Other customary additives can also be incorporated into the coating solution or coating dispersion which change the spectral sensitivity or electrophotosensitivity of the recording material.

Conventional known sensitizers can be used to sensitize the photoconductors used according to the invention may be used, for example those known from U.S. Patent 3,250,615 Pyrylium, thiapyrylium and selenapyrylium dye salts, fluorenes, e.g. B. 7,12-Dioxo-13-dibenzo- (a, h) -fluorene, 5,10-Dioxo-4a-ll-diazabenzo (b) fluorene and 3,13-Dioxo-7-oxadibenzo- (b, g) fluorene, and also the aggregate-forming sensitizers of the type known from Belgian patent specification 705 117 Type, also aromatic nitro compounds of the

is U.S. Patent 2,610,120, which Anthrones known from US Pat. No. 2,670,284, those known from US Pat. No. 2,670,286 Quinones, the benzophenones known from US Pat. No. 2,670,287, which are known from

ao U.S. Patent 2,732,301 known thiazoles, also mineral acids, carboxylic acids, for example Maleic acid, dichloroacetic acid, trichloroacetic acid and salicylic acid, as well as sulfonic acids and phosphoric acids and a wide variety of dyes, e.g. B. Cyanine Color

iS materials, including carbocyanine dyes, merocyanine, diarylmethane, thiazine, azine, oxazine, xanthene, phthalein, acridine, azo and anthraquinone dyes, and mixtures thereof.
Pyrylium, selenapyrylium and thiapyrylium dye salts and cyanine dyes, including carbocyanine dyes, have proven to be particularly advantageous sensitizers for sensitizing the photoconductors used according to the invention.
If a sensitizer is used for the production of the electrophotographic recording material according to the invention, it has proven to be expedient to mix it into the coating material in customary concentrations and to distribute it thoroughly therein. If necessary, however, the sensitizer can also be applied by other customary known methods.

However, the use of a sensitizer is not absolutely necessary. Since, however, already relatively low concentrations of sensitizers a

♦ 5 substantial increase in the sensitivity of the photoconductive To effect layers, it has proven to be useful to use sensitizers. the In individual cases the most favorable concentration of sensitizer can be very different in purity. In individual cases

The most favorable concentration can depend on the photoconductor used in the individual case and the specifically used one Depend on the sensitizer.

In general, it has proven to be useful to use sensitizers in concentrations of about 0.0001 up to about 30 percent by weight, based on the weight of the photoconductive layer, preferably ir Concentrations from about 0.005 to about 5.0 weight percent based on the weight of the photoconductive Layer to use.

The customary known binders can be used to produce the photoconductive layers which are known for the Het position of photoconductive layers. With these polymeric bandages agents are film-forming, hydrophobic

Polymer materials with good electrical insulating properties and corresponding dielectric properties Strengths. For example, for the production of an electrophotographic recording material according to de

ίο

Io

Invention as a binder for the photoconductive ethylene terephthalate or polystyrene, on the im Va layer for example: kuum a metal layer, for example a layer

Styrene-butadiene copolymers; Silicone resins; vapor-deposited from silver, nickel or aluminum Styrene alkyd resins; Silicone alkyd resins; Soy alkyd has been.

resins; Polyvinyl chloride; Polyvinylidene chloride, vinyl 5 Particularly advantageous conductive layer carriers, condensate chloride-acrylonitrile copolymers, Polyvinyls are produced by applying a transacetate, vinyl acetate-vinyl chloride copolymers, parent film support, for example made of poly-polyvinylacelate, z. B. polyvinyl butyral, polyacrylic ethylene terephthalate, a layer of a binding acid and polymethacrylic acid esters, e.g. B. Polymethyl- agent is applied, in which a semiconductor methacrylate, poly (n-butyl methacrylate) and poly io is dispersed. Further advantageous conductive layers For example, isobutyl methacrylate, polystyrene, nitrated polystyrene can be made from the Polymethylstyrene, isobutylene polymers, polyester, sodium salt of a carboxy ester lactone, a malt. B. Poly-ethylene-co-alkylene-bis-Ulkylenoxyaryl) - acid anhydride-vinyl acetate copolymer from phenylenedicarboxylate], phenol-formaldehyde resins, copper iodide and the like. Such conductive layers and Ketone resins, polyamides, polycarbonates, polythio- 15 processes for their production are for example from carbonates, poly [ethylene-co-isopropylidene-2,2-bis- den USA. Patents 3,007,901, 3,245,833 and (ethylene oxyphenylene) - terephthalate copolymers - 3,267,807 known.

sate of vinyl haloarylates and vinyl acetate, e.g. B. Preferably, the substrate of the electro-

Copolymers of vinyl-m-bromobenzoal and photographic recording material after vinyl acetate, and the like. In the invention, such binders consist of a transparent substrate. Commercially available. Their production is carried out in the The electrophotographic recording materials

various patent specifications are described in more detail. Materials according to the invention can be used in the context of for example, the production of styrene-alkyd resins is conventionally known electrophotographic processes U.S. Patents 2,361,019 and 2,258,423 may be used. One of those procedures is this known. If necessary, so-called xerographic copying processes can be used as binders for the 25. At the manufacture The photoconductive layers are also subjected to an electrophotographic process in this process Substances such as paraffins or mineral waxes, drawing material initially stored in the dark be used. and uniformly electrostatically charged, for example

To prepare the coating compounds, this can be done by means of a corona charge. The most diverse conventional known organic charges are due to the insulating solvents are used, for example benzene, properties of the photoconductive layer in the dark Toluene, acetone, 2-butanone, chlorinated hydrocarbons retained, d. H. due to the low conductivity, z. B. methylene chloride and ethylene chloride, ability of the layer in the dark. The ether so past, z. B. tetrahydrofuran, or mixtures of the ridden recording material can then be image-accurate like solvent. 35 are exposed, for example in the context of

It has proven to be useful if the contact copying process or by projecting Concentration of the photoconductor in the photoconductive an image with the help of a lens or a lens-capable layer at least 1 percent by weight, be systems or warped in the context of reflex or bireflex on the weight of the photoconductive layer, leaving an electrostatic latent image in the amounts to. 40 photoconductive layer is produced in that

The upper concentration limit can be very different from the electrostatic charges selectively from the upper one being. It can be around 99 percent by weight. surface of the photoconductive layer can be derived. It has proven advantageous to first apply the photoconductor to the photoconductive layer in concentrations from 10 to about 60 percent by weight, charges introduced are withdrawn on exposure based on the weight of the photoconductive layer, 45 speaking of the intensity of the irradiated radiation to use. derived. After the image-appropriate exposure shows

The layer thickness of the photoconductive layers on the surface of the electrophotographic print corresponds to the layer thickness of conventional, known electrophotographic recording materials, thus a charge pattern or trophotographic recording materials. As a latent electrostatic image , it has proven expedient if the layer is wound or transferred to the image receiving layer, measured wet, about 0.0025 to about 0.025 cm, and can be developed here. In particular, it is 0.005 to about 0.015 cm. The winding can either have the charged thickness or not, but can also be below or above the charged areas of the photoconductive layer according to the values given. winds, ie made visible, which is done with the aid of a so-called toner, ie particles of optical drawing materials according to the invention, the density. These so-called toner particles, known electrically conductive layer carriers, can be used in the form of dust or powder, the use of which is used for production, and generally consist of electrophotographic recording materials consisting of a pigment in a hard carrier or known. The various binders may be mentioned, for example. In a particularly advantageous manner, the most conductive papers, aluminum-paper-laminates, such toners can be used with the aid of a magnetic brush, metal foils, for example aluminum and, for developing the latent electrosta-zinc foils produced, metal plates, for example from aluminum images. Such development vernised plates using a nium, copper, zinc and brass, as well as a galvanomagnetic brush, and also layer supports, which are used, for example, from the following USA 439, 2 786440, 2 786 441, graphic recording materials used 2,811,465.2 874063.2 984163.3 040 704.3 117 support made of, for example, cellulose acetate, poly and the Reissue patent Re 25 779 known.

The latent electrostatic images initially generated can, however, also be recorded in the usual way develop fluently. In such development processes, liquid developers are used, in which the toner particles are used in an electrically insulating carrier liquid will. Development methods of this type are disclosed, for example, in U.S. Pat. No. 2,297,691 and Australian Patent 212 315 known.

In the case of the known dry development processes, it has proven advantageous to achieve more permanent Copies to use such toners the particles of which have a resin of low melting point. By warming or heating the powder image initially obtained, this resin melts brought and melted on the base. In this way there is a permanent liability of the Toner particles achieved on the surface of the photoconductive layer. On the other hand, however, it is too possible to first apply the charge image or the powder image initially obtained to an image receiving layer, ζ. B. from paper to transfer, whereupon the transfer image obtained for final copy or final copy is further processed. Such development processes are, for example, from the USA. Patent- »5 Writings 2,297,691 and 2,551,582 and the journal "RCA Review", Volume 15 (1954), pp. 469 to 484, are known.

Optionally, the electrophotographic recording material may have more than one photoconductive one Have layer, these layers may optionally be separated by other layers. the Layer supports can not only be transparent, but also opaque.

The photoconductors used according to the invention can be produced by customary known synthesis methods will. In the following, the production of some photoconductors used according to the invention will first be described are described in more detail.

40 A) 2,2-bis (4-N, N-diethylaminophenyl) propane (11)

A mixture of 29.0 g of acetone, 100 ml of concentrated hydrochloric acid and 150 g of N, N-diethylaniline was heated to reflux temperature. It was then made alkaline, whereupon unreacted N, N-diethylaniline was removed by steam distillation. The organic residue was extracted with benzene, whereupon the benzene extract was dried _{over CaCl 2.} The solvent was then evaporated. The crystalline residue was then recrystallized from ethanol. 1.2 g of the reaction principle with a melting point of 84.1 to 84.9 ° C. were obtained.

Analysis for Calculated found

₃₄

C81.7, H 10.1, N 8.28%

C 81.6, H 10.1. N 8.3%.

55

B) 1,1 -Bis- (4-N, N-dimethylaminophenyl) -

cyclohexane (III)

The compound was obtained by condensing cyclohexanone with N, N-dimethylaniline in concentrated hydrochloric acid according to the method described by JV B rau et al in Ann. 472, 29 (1929). After purification by column chromatography and recrystallization from cyclohexanone, the compound with a melting point of 156.0 to 157 ° C. was obtained.

Analysis for C ₂₂ H ₃₀ N ₂ :
Calculated
found

C 82.1, H 9.22, N 8.70%;
C 82.7, H 8.8, N 8.70%.

C) 2,2-bis (4-N, N-diethylaminophenyl) butane (IV)

A mixture of 36 g of 2-butanone, 149 g of N, N-diethylaniline, 70 ml of concentrated hydrochloric acid and 12.5 ml of ethanol was poured into several pressure bottles, whereupon these were heated on the steam bath. The contents of the bottle were then subjected to steam distillation, after which the residue was made alkaline by the addition of solid sodium hydroxide and again steam distilled. The remaining organic residue was then extracted with benzene, whereupon the benzene extract was dried over magnesium sulfate. The benzene was then distilled off. A total of 28.0 g of reaction product with a boiling point of 160 to 202 ^° C. at a pressure of 0.2 mm was obtained.

Analysis for C ₂₄ H ₃₆ N ₈ :
Calculated ... C 81.7, H 10.3, N 7.97%;
found ... C81.8, H 9.8, N8.1%.

D) 2,2-bis- (4-N, N-diethylaminophenyl) -heptane (V)

A mixture of 114.2 g of 2-heptanone, 300 g of N, N-diethylaniline, 140 ml of concentrated hydrochloric acid and 25 ml of ethanol was heated to reflux temperature. The reaction mixture was then made alkaline and steam distilled. The remaining organic residue was extracted with benzene, washed with a brine and dried over magnesium sulfate. The reaction mixture was then concentrated under reduced pressure. The residue was then distilled, collecting a fraction with a boiling range of 180 to 233.5 ° C. at a pressure of 0.3 mm. Crystals separated from it when left to stand. This fraction was triturated twice with cold methanol, whereupon the precipitated reaction product was recrystallized three times from methanol-ethyl ether solutions. A total of 16.7 g of reaction product with a melting point of 42.0 to 44 ° C. were obtained.

Analysis for
Calculated
found

C82.18, H 10.73, N 7.10%; C 81.9, H 10.7, N 7.3%.

E) 1,3,3-Tris- (4-N, N-diethylaminophenyl) -butane (VI)

A mixture of 132 g of 4-hydroxy-2-butanone 450 g of Ν, Ν-Dilthylanihn, 150 ml of concentrated hydrochloric acid and 20 ml of ethanol was heated to reflux temperature. The reaction mixture was then distilled with steam, whereupon the residue was made neutral with sodium hydroxide. It was then distilled again with steam. The organic residue was then taken up in ethyl ether and _{dried over Na 2} CO ₈ , whereupon the solvent was distilled off. The return Stan <was then in order to remove one at a Drucl of 1.3 mm of mercury below 150 ⁰ C it Denden distilled fraction of the distillation recycle Stanistreet was taken up in hot ethanol. From de

d 14

ethanol solution separated on cooling I) l, l-bis (4-N, N-diethylaminophenyl) -

the reaction product from. It was twice from 4-methylcyclohexane (X) Nitromethane uncrystallized. There were a total of

20 g of reaction product with a melting point of A mixture of 112.0 g of 4-methylcyclohexanone,

76 to 77 ° C. 5,300 g of N, N-diethylaniline and 110 ml of concentrated

f r · η w hydrochloric acid was brought to reflux temperature

Analysis door c _M H ₄ , rv heated. The reaction mixture was then through Calculated ... C 81.7, H 9.8, NM ^; Addition of sodium hydroxide made alkaline and

found ... C 81.5, H 9.9, N 8.6 / _o . steam distilled. The organic residue was with

F) l, l-bis (4-N, N-diethylaminophenyl) - » ^Ben f ^o1 _t ^e f" ^ah i ^rt _n ^u " ^{d 0} ^ f. Sodium carbonate

ν lohexane (VII) dries. The solvent was then removed

* steams. The solid residue became from nitromethane

A mixture of 98.0 g of cyclohexanone, 298 g recrystallized. There were 75 g of a colorless Ν, Ν-diethylaniline, 92 ml of concentrated Chlorwasser- crystalline reaction product having a melting hydrochloric acid and 25 ml of ethanol was reflux for 15 point of 105 to 106 ⁰ C obtained heated temperature. The reaction mixture was then made alkaline analysis for CHN · whereupon the organic layer, _RMW i, _nrt ^? r « _{H Hiri} , _N7n o.,

which had deposited, extracted with benzene ^Bere ^ ⁿ * ··· £ 82.6, H 0.2, N 7.13 / ..

would. The benzene solution obtained was then found ... C 82.7, H 10.3, N 6.9 / _o .

washed with water and over magnesium sulfate .0 _J} i, i_ _B is- (4-N, N-diethylaniinophenyl) -

dried. The benzene was then distilled off, 3-methylcyclohexane (Xl)

which was then diluted with methanol. When the solution was left to stand, the reaction product separated from a mixture of 100 g of 3-methylcyclohexanone, in the form of a solid mass, which recrystallized from a 266 g of Ν, Ν-diethylaniline, 125 ml of concentrated chlorine mixture of methanol and ethyl acetate and 25 hydrochloric acid 25 ml of ethanol was put back on. A total of 93.0 g of reaction flow temperature was heated. The reaction mixture was made product with a melting point from 89.5 to 90.5 ⁰ C while alkaline and steam distilled. The received. organic residue was extracted with benzene,

washed with a saline solution and dried over magnesium sulfate. The residue was then concentrated _{in vacuo.} The residue was ^ _1n j cooling, whereupon it is stirred with methanol

G) 1 l-bis (4-N, N-di-n-propylaminophenyl) - ^ "^ ^The _x i ^ ^tren ₁ ⁿ t ^e _u ^fc ? ^Te residue was then

u; 1,1 ο «. ^v ', _ohexaI [JYJj ₁ ) vji _{from a} methanol-ethyl acetate mixture

^y 35 sated. There were a total of 88 g of reaction product

A mixture of 177.3 g Ν, Ν-di-n-propylaniline, a melting point of 83.6 to 85.1 ⁰ C obtained. 49.0 g of cyclohexanone, 70 ml of concentrated chlorine analysis for C ₁₇ H ₄₀ N .: hydroic acid and 10 ml of ethanol was calculated on the back of TR? Fi brain isi7ifto /.

heated river temperature. The reaction mixture was * ™ * J * -C 82.6, H 0.3, N 7.16 / ..

then made alkaline and the organic phase 40 S ^eiunaen · * - ^«J M ^H" M, N 'V / o was extracted with benzene. The benzene extract was _{K) U. B} is- (4-N, N-diethylaminophenyl) -

then washed with a salt solution and dried over 4- (l'-methylpropyl) <yclohexane (XH)

Magnesium sulfate dried Then the ^{J v FJf} ^ ^CM11 ^ "' Benzene evaporated. The residue was then A mixture of 123.5 g of 4- (l'-methylpropyl) -

Distilled 119.5 g of reaction product with «cyclohexanone, 239 g of Ν, Ν-diethylaniline, 100 ml of a boiling point of 180 to 245 ° C at a pressure centered hydrochloric acid and 25 ml of ethanol obtained from 0.2 mm of mercury. was heated to reflux temperature, whereupon the

* - r η ν reaction mixture made alkaline and steam-

Analysis for ^ 30 "« ",. Was distilled. The residue was on standing Calculated ... C 82.8, H 1U, CO, H «V» / _o , _So solid. He was washed with water and taken out of one

found ... C 82.6, H 1U, D, at 0, / / _o . Ethanol-ethyl acetate mixture recrystallizes on this

Analysis for (J, .H ₈₈ N ₁ : H 10.12, N 7.4%; Calculated .. . C 82.49, H 10.3, N 7.6%. found .. . C 82.7,

Analysis for

r ^ . . -, -, r. Analysis for Cj ₀ HmN-:

A mixture of 98.0 g of cyclohexanone, 270 g of 55 η ™ - ^ -, r _R , c _Ηιη7 ν, Äthvl-N-methylaniline, 140 ml of concentrated chlorine- Calculated ... C 83.5, H 10, /, N,%

SSSSlSLa 25 Kl ethanol was converted back to C 82.8, H 10.7, N 6.6%.

Flußtempcratar heated, whereupon the reaction mixture _L) i, i- _B is- (4-N, N-diethi1aminophenyl) -

S55 / SSL3 ( ¹ A ¹¹ SSSSS? ^E ? "^ IM '^^ hlbll

S55 / SSS

quickly crystalline. It was washed with water A mixture of 105 g 4- <r, r, 3 ', 3'-tetramethyl-

and from an ethanol-benzene mixture recrystallized butyl ^ cyclohexanone, 149 g Ν, Ν-diethylaniline, 60 ml

sated. There were 109.7 g of reaction product with a concentrated hydrochloric acid and 15 ml of etha

Melting point of 122.5 to 123.4 ° C obtained. nol was heated to reflux temperature

65 reaction mixture was then made alkaline and

Analysis for C ₁₄ H ₃₁ N ₁ : Steam distilled. The organic residue was with Calculated ... C 82.25, H 9.78, N 7.99%; Benzene extracted, washed with a brine and

found ... C 82.4, H 9.8, N 8.3%. Was then dried over magnesium sulfate

■ ier

: ratur

on,
torckrde
)he

mnd
de
irt in
Ii iit

the solvent evaporated. A small portion of the residue was distilled. A crystalline solid mass was obtained by triturating a fraction with a boiling range from 217 to 268 ^° C. at a pressure of 0.3 mm with ethanol. Most of the residue was also stirred up with ethanol and inoculated with the crystals obtained. In this way, a total of 17.5 g of reaction product having a melting point of 91.1 to 93 ° C. was obtained.

Analysis for C ₃₁ H ₅₁ N ₂ :
Calculated ... C83.1, H 11.1, N 5.7%;
Found ... C 82.8, H 10.7, N 6.4%.

M) 1,1-bis (4-N, N-diethylaminophenyl) -3,4-dimethylcyclohexane (XlV)

A mixture of 170 g of 3,4-dimethylcyclohexanone, 400 g of N, N-diethylaniline, 135 ml of concentrated hydrochloric acid and 20 ml of ethanol were brought to reflux temperature heated. The reaction mixture was then steam distilled, whereupon the residue up to Neutrality sodium hydroxide was added. It was then steam distilled again. The organic one The residue was extracted with toluene and dried over sodium carbonate. Subsequently was the solvent evaporated. The residue was distilled, one at 215 ° C and a pressure fraction distilling from 0.12 mm of mercury was collected and recrystallized from ethanol. A total of 55 g of reaction product with a melting point of 92 to 93 ° C. were obtained.

Analysis for C ₂₈ H ₄₂ N ₈ :
Calculated ... C 82.8, H 10.3, N 6.89%;
Found ... C 82.9, H 10.7, N 7.1%.

N) 1,1-bis (4-N, N-diethylaminophenyl) -3,5-dimethyl-yclohexane (XV)

A mixture of 100 g of 3,5-dimethylcyclohexanone, 240 g of N, N-diethylaniline, 80 ml of concentrated hydrochloric acid and 10 ml of ethanol was heated to reflux temperature. The reaction mixture was then steam distilled to remove excess ketone, whereupon it was neutralized and steam distilled again _{to remove excess N 1} N diethylaniline. The organic residue was then extracted with ethyl ether and dried over sodium carbonate. The solvent was then evaporated. The residue was then distilled. A fraction boiling at a pressure of 0.72 mm of mercury at 225 ° C was collected. It was taken up in hot ethanol and cooled. 10 g of crystalline reaction product with a melting point of 89 to 90 ^° C. separated out.

Analysis for C ₂₈ H ₄₂ N ₂ :
Calculated ... C 82.8, H 10.3, N 6.89%;
found ... C 82.7, H 10.6, N 7.1%.

O) 2- [4,4-bis <- (4-N, N-diethylaminophenyl) -cyclohexyl] -2-cyclohexylpropane (XVl)

A mixture of 111 g of 4- (2-CycIohexylisopropyl) -cyclohexanone, 149 g of Ν, Ν-diethylaniline, 50 ml of concentrated hydrochloric acid and 10 ml of ethanol was used heated to reflux temperature. The reaction mixture was then steam distilled to remove any unreacted Remove ketone. Then the reaction mixture was made by adding sodium hydroxide neutralized and steam-distilled again to remove unreacted Ν, Ν-diethylaiiilin. The remaining one organic residue was then extracted with ethyl ether and dried over sodium carbonate. The solvent was then evaporated. The residue was dissolved in cyclohexanone and filtered through neutral aluminum oxide. The aluminum oxide was made by pouring several servings over it Cyclohexanone eluted. The combined filtrates were then evaporated. The solid residue was recrystallized from ethanol. There were a total of 50 g of reaction product with a melting point of 110 to 111 ° C obtained.

Analysis for C ₃₅ H ₅₄ N ₂ :

Calculated ... C 83.7, H 10.7, N 5.58%;
Found ... C 83.4, H 10.7, N 5.8%.

P) l, l-bis (4-N, N-diethyIaminophenyl) - ^ao cyclopentane (XVlI)

A mixture of 168 g of cyclopentanone, 600 g of Ν, Ν-diethylaniline, 200 ml of concentrated hydrochloric acid and 10 ml of ethanol was refluxed

»5 temperature heated. The reaction mixture was then Steam distilled to remove excess ketone, neutralized and again to remove excess Ν, Ν-diethylaniline steam distilled. The organic residue was taken up in benzene and dried over sodium carbonate. The solvent was then evaporated. The residue got stuck while standing. It was recrystallized from ethanol. A total of 25 g of reaction product with a melting point of 99 to 100.degree. C. were obtained receive.

Analysis for C ₂₅ H ₃₈ N ₂ :

Calculated ... C 82.4, H 9.88, N 7.68%;
Found ... C 82.0, H 10.0, N 7.7%.

Q) l, l-bis (4-N, N-diethylaminophenyl) -

cycloheptane (XVIII)

A mixture of 100 g of cycloheptanone, 266 g of Ν, Ν-diethylaniline, 100 ml of concentrated water of chloride

chemical acid and 25 ml of ethanol were heated to reflux temperature. The reaction mixture was then made alkaline and steam distilled. The residue was then extracted with benzene and washed with a brine solution and dried over magnesium sulfate. The solvent was then evaporated. The residue solidified on trituration with cold methanol. The solid residue was then recrystallized from a mixture of methanol and ethyl acetate. A total obtain 12.3 g of reaction product having a melting point 76.0 to 76.9 C ^0.

Analysis for C ₂₇ H ₄₀ N ₂ :

Calculated ... C 82.6, H 10.26, N 7.35%;
Found ... C 82.6, H 10.1, N 6.9%.

R) 2,2-bis- (4-N, N-diethylaminophenyl) norbornane (XIX)

A mixture of 97 g of 2-norbornanone, 300 g of Ν, Ν-diethylaniline, 140 ml of concentrated hydrochloric acid and 25 ml of ethanol was heated to reflux temperature. The reaction mixture was then made alkaline and steam distilled. the

Analysis for C ₂₇ H ₃₁₁ N ₃ : H 9.82, N 7.18 (1
/O Calculated ... C83.0, H 9.4, N 7.6 ° found ... C82.8,

organic residue, which solidified quickly, was applied. The recordings obtained were filtered off, washed with water and made of a material were then dried at 32.degree. Recrystallized from a mixture of ethanol and benzene. It schüeßend 13.5 g of reaction product they were by means of a negative Cowurden been charged with a Rona discharge obtained until the Uberflacnen melting point of 120.0 bi "122 ⁰ C. 5 potential as determined by an electrometer

_was 600 volts. The recording materials were then exposed to a tungsten light source at 3000 ° K through a stepped gray wedge. In the exposure, a decrease in the Oberflächennotpntiik was carried out every one step of the gray wedge on ur-S) 4,4,4 \ 4'-tetrakis (4-N, N-diäthylaminophenyll) - ¹⁰ ^ ScL _{n o} K potential to a lower potential K, bicyclohexane (XX) _d ^ ert _{SEN exact W} from on the recording

A mixture of 49.0 g of 4,4'-bicyclohexanone, material amount of incident light in mete; -Candle-240 g of N, N-diethylaniline, 100 ml of concentrated chlorine-seconds depended.

hydrochloric acid and 10 ml of ethanol was applied to rear, the ₅ OberHachenfiußtemperatur then were heated in a diagram. The mixture was then potential V as a function of the logarithm which makes the exposure for each individual step of the stepped gray wedge acidic by the addition of hydrochloric acid and extracted with methylene chloride. The applied. .

The aqueous layer was obtained by adding sodium. The so-called sensitivities were determined

hydroxyd neutralizes. The exiting organ- 20 in the slack area, which is the numerical expression niche precipitate was filtered off, dried and multiplied by 10 * by the inverse of the Beaus Xylene recrystallized. A total of 85 g of exposure in meter-candle-seconds were represented Reaction product with a melting point of 264 is required to have the surface potential of 600 up to 265 ° C. to decrease to 100 volts.

Analv, e for Γ HN ² S The results obtained are shown in Table II.

Calculated ... C 82.9, H 9.8, N 7.42%; compiled:

Found ... C 83.3, H 9.9, N 7.6%. lukewarm 11

T) 2,2-bis- [4,4-bis- (p-N, N-diethylaminophenyI) -

cyclohexyl] propane (XXl) ³ °

A mixture of 43.0 g of 2,2-bis- (4-oxo-cyclohexyl) -propane, HOg Ν, Ν-diethylaniline, 44 ml of concentrated hydrochloric acid and 25 ml of ethanol
was heated to the re-nut temperature. The reaction 35
The mass was then made alkaline and steam distilled. The aqueous phase was then of
decanted from the semi-solid organic residue,
whereupon the residue washed with water and off
was recrystallized from an ethanol-benzene mixture. 40 B eis ρ ie 1 2

There were a total of 18.0 g of reaction product

obtained a melting point of 210.8 to 211.5 ° C. The procedure described in Example 1 was followed

a, ... ^ τ, χι repeated, with the exception, however, that this time as

Analysis for L ₅₆ H ^ N ,,: sensitizer 2 ₎ 6-bis- (4-ethylphenyl) -4- (amyIoxyphe-

öerecnnet ... c 82.9, HU) ₁ I, N /, udz _0, was _{45 n} yivthiapyryliumperchlorat used. It was

found ... C 82.8, H 10.1, N 7.1%. get the appropriate favorable sensitivities.

The following examples are intended to further illustrate the invention. Accordingly, favorable results have then been obtained

illustrate. obtained when the sensitizer is 2,4-bis- (4-ethyIphenyl) -

Example 1 6- (4-styrylstyryl) -pyrylium perchlorate was used.

5c R p j ^ η Ϊ p 1 * i

A mixture of the following _v ...,. '. ..
Ingredients were first placed in a mixer (Vergieicnsoeispiei;
Prescribed method using a PHOTOL, 0gP _O LY (4,4'-iso _P ropylidendiphen _y lencarbonat) 55 head of from British Patents 980,879 as a binder ·: 30 minutes at room temperature shear forces For comparison purposes, which was beausgesetzt in Example 1 ^{and 984964 of} known type are repeated. The ver-0.025 g of 2,6-Dip'henyl-4- (4-dimethylaminophenyl) - _u ^applied photoconductor comprised bis (N, N-dirnethylthiapyryliumperchlorat as Sensibilisierungsfarb- aminophenylmethane). The measured sensitivity was 500, ie the sensitivity of this ^{drawing material to 96 g of dichloromethane So} was considerably below the sensitivity of the recording material according to the invention in various proportions of the heterogeneous materials obtained.

In each case, 0.25 g of the mixture in the range was then added
photoconductors listed in the following tables. 1 uL '
The coating compositions obtained were then in 65 (comparative example)
a layer thickness of 0.010 cm, measured wet, for comparison purposes, a layer support made of polyethylene terephthalate, onto which a conductive nickel layer had previously been vapor-deposited using 1,1-bis (4-N, N-diethylamino-2-methylphenyl ) -l-phenylmethane

Photoconductor No. sensitivity II 1050 IV 1100 V 1050 VII 900 VIII 800 IX 1000 XVII 1000 XVIIl 800

/ I *

manufactured as a photoconductor The recording material had a sensitivity of 458. The photoconductor used is from German Patent 1,273,900 known.

Example 5

According to the procedure described in Example 1, further coating compositions were prepared The photoconductors I to XXIV listed in Table I were used for their production.

In a darkened room, the surfaces of the electrophotographic recording materials obtained were charged to a potential of about -600 volts by means of a corona discharge.

The charged recording materials were then covered with a transparent template, which for areas opaque to light. The recording materials were then through the template by means of an incandescent lamp with a lighting intensity of about 807 lux (75 meter candles) for 12 seconds long exposed.

The electrostatically charged recording materials obtained were then processed in the usual manner developed by cascade development, a mixture of negatively charged black, thermoplastic toner particles for cascade development on glass beads that served as carriers for the toner particles.

Excellent reproductions of the original were obtained in all cases.

Correspondingly favorable results were obtained when a conventional known one was used for development liquid developer was used.

As stated above, an electrophotographic recording material can be made according to the invention have one or more photoconductive layers. If the recording material has several photoconductive layers, these can be adjacent to one another or by a layer of an insulating layer Fabric to be separate from each other. An insulating layer can also be used between the photoconductive layer or layers and the conductive layer support be arranged. A cover layer can also be applied to the photoconductive layer. Finally, it is also possible to place a photoconductive layer on a transparent, insulating layer support and applying a transparent conductive layer either to the photoconductive layer or to the rear side of the support.

Example 6 (Comparative example)

Seven different photoconductors were tested for resistance to exposure to white and ultraviolet light tested. For this, 0.2 g of photoconductor in 5.6 ml of methylene chloride and 1.4 nil Dissolved dioxane, whereupon the resulting solutions were mixed with 0.8 g of poly (vinyl-m-broniobenzoate) as a binder.

The coating compositions were then applied to white conductive paper backing in such a way that photoconductive layers with a layer thickness of 10 microns measured dry were obtained, ίο The photoconductors consisted of:

A 4,4'-bis (diethylamino> -2 ^ '- dimethyl-triphenylmethane (according to German patent 1 237 900 and U.S. Patent 3,542,547); * 5 B 4-diethylaminotetrapbenylethane (according to Belgian patent specification 696114 and British patent specification 1172160);

C bis (diethylamino) tetraphenyhnethane (according to Belgian patent specification 696114 and British patent specification 1172 160);

D l, l-bis (4-diethylaminophenyl) cyclohexane

(according to the invention); E 2,2-bis (4-diethylaminophenyr) propane

(according to the invention); as F l, l-bis (4-diethylaminophenyl> 4-methylcyclo-

hexane (according to the invention); G 2,2-bis (4-diethylaminophenyl) heptane (according to the invention).

Sections of the recording materials produced were exposed for 10 minutes with a 500 watt nitrophot lamp placed at a distance of 26.7 cm. Other sections of the recording materials were used for 10 minutes

exposed to a UV lamp set up at a distance of 5 cm. The following results were obtained:

40 Photo
ladder hue
the fresh
manufactured Shade of material
after exposure with UV lamp Materials Nitraphot lamp Strong green A. White Strong green Light brown 45 β White Light brown Brown C. White Brown White D. White White White I. White White White ϊ j white White White 50 ^ White White

The results obtained show the excellent light resistance of the present invention used photoconductors compared to known photoconductors.

Claims (3)

ι 2 according to the radiated energy reduced claims: is. This creates a latent electrostatic image which develops with a toner 1. Elektrophotographisclies recording ma- can be. The toner particles can be in material with a substrate and a photoconductive 5 an insulating liquid applied capable layer, which as a photoconductor is a bis- (N, N-di- or on a dry carrier powder. alkylaminophenyl) methane, a binder and where it is possible to either use the toner particles if necessary, a sensitizing dye removes the charged or non-charged areas of the photo, characterized in that the conductive layer is deposited. The ones on the photoconductive layer as a photoconductor a ver io photoconductive layer precipitated toner particles bond of the formula can then, for example, by the action of Heat, pressure or solvent vapors perma- £ ρ nent be fixed or on an image receiving R ₁ R ι ⁷ IR ₃ material are transferred, in which they in ent- X ^ ^ X ⁼⁼⁼ \ J- / I ^ χι * 5 can be permanently fixed in a meaningful way. ■ / γ ^. "~. On the other hand, it is also possible to do that initially Rg R ₄ generated latent electrostatic image to transfer to an image receiving material and develop this. For the production of electrophotographic stays in which R ₁ , R ₂ , R ₃ and R ₄ each equal to an ao drawing materials, a wide variety of optionally substituted alkyl groups with 1 to organic and inorganic compounds as 18 carbon atoms, R ₅ and R ₆ each equal to photoconductors can be used . a hydrogen or halogen atom or a So it is e.g. B. from the British patents optionally substituted alkyl or alkoxy 984 965 and 980 879 of the Belgian patent group and R, and R "each equal to one against-» 5 696 114, the German Auslegeschrift 1 237 900 and optionally substituted alkyl group with 1 to the German Offenlegungsschrift 1,497,083 known, 18 carbon atoms or a photoconductor, if necessary, diaryl and triaryl compounds, ins- substituted cycloalkyl group or together special the l.euko bases of triarylmethane dye equal to an optionally substituted cyclo- substances, z. B. the leuco base of Knstaüviolett or are alkylidene group. 30 the leuco base of malachite green, further z. B. Up to 2. Recording material according to claim 1, da- (4-dimethylaminophenyl) -phenylmethane and bis, characterized in that the photoconductive (4-dimethylaminophenyl) -methane to be used.
Layer as photoconductor 2,2-bis- (4-N, N-diethyl-) Optically clear aminophenyl) propane, 2,2-bis- (4-N, N-diethyl- or transparent photoconductor electroaminophenyls are particularly advantageous ) -butane, 2,2-bis- (4-N, N-diethylamino- 35 photographic recording materials have been shown to be phenyl) -heptane, l, l-bis- (4-N, N-diethylaminophe- because these may be transparent nylJ-cyclopentane or l-bis- ^ N-ethyl-N-ynethyl layer support can be exposed and, because the aminophenyO-cyclohexane contains 3. Recording material according to claim 1, there in various ways in devices of the various characterized in that the photoconductive 40 most constructions can be used. A Layer to IC up to 60 percent by weight from the further advantage of such recording materials Photoconductor, from 0.005 to 5 percent by weight, consists in the fact that it verdem several times if necessary Sensitizing dye and the rest up are reversible, d. that is, after removing the pre-100 Weight percent consists of the binder. existing toner from an initially generated image, 45 for example by transferring or cleaning, are ready for use again. A disadvantage of many of the known electrophotographic recording materials with organic Photoconductors, however, are still sensitive to their sensitivity The invention relates to an electrophotographic 50 leaves something to be desired and that the recording recording material with a layer support and voltage materials due to insufficient photosensitivity of a photo-conductive layer which, as a photoconductor, easily discolor the photoconductor.
Bis- (N, N-dialkylaminophenyl) methane, a binder The object of the invention is to provide an electrophotographic and optionally a sensitizing dye; Contains recording material with one layer. 55 carrier and a photo-conductive layer, which is known as it is, for example from the USA.-Patent Photoconductor a bis (N, N-dialkylaminophenyl) methane, 297 691, in the context of electrophotographic association a binder and optionally a sensitizing recording materials with contains a layering dye which is characterized by a carrier and a photo-conductive layer applied thereon, compared to comparable electrophotographic layers, the electrical resistance of which corresponds to the electro- and light-resistance impinging on this layer.
magnetic radiation changed to use. It has been found that very specific tetra-processing of such electrophotographic up-substituted bis (N ₁ N-dialkylaminophenyl) methane drawing materials is usually carried out as an excellent photoconductor for the production of electrodas this in the dark, usually after one photographic recording materials are suitable,
know dark adaptation, initially uniformly. The object of the invention is thus about a charged, whereupon they are exposed imagewise to the electrophotographic recording material, whereby the potential of the surface charge is a support and a photo-conductive layer,